Tetrahedron p. 12115 - 12129 (1997)
Update date:2022-08-02
Topics:
Kurose, Noriyuki
Takahashi, Tamiko
Koizumi, Toru
The first synthesis of optically pure selenuranes 1 has been accomplished by utilizing 2-exo-hydroxy-10 bornyl group as a chiral ligand Complete retention of the configuration has been observed in alkaline hydrolysis of 1 to give selenoxides 2. The structure of 1 and 2 has been fully established by X-ray crystallography. [2,3] Sigmatropic rearrangement of allylic selenoxides 2 gave the corresponding allylic alcohols 3 with up to 88% enantiomeric excess (ee). The [2,3] sigmatropic rearrangement of allylic selenoxides 2 progresses predominantly via an endo transition state.
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